


Let's Do It Again

by GetOutOfMyHead



Category: Supernatural
Genre: Barebacking, Brother-Sister Relationships, Brother/Sister Incest, Double Penetration, Double Vaginal Penetration, F/M, Incest, Multiple Orgasms, Original Male Character - Freeform, Phone Sex, Porn, Sibling Incest, Smut, Top Dean Winchester, Vaginal Fingering, Vaginal Sex, Wincest - Freeform
Language: English
Status: Completed
Published: 2020-04-01
Updated: 2020-04-09
Packaged: 2021-02-28 22:47:42
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,147
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23434891
Author URL: https://archiveofourown.org/users/GetOutOfMyHead/pseuds/GetOutOfMyHead
Summary: Dean walks in on his sister having phone sex with her boyfriend.
Relationships: Dean Winchester/Original Female Character(s), Dean Winchester/Sam Winchester, Sam Winchester/Original Female Character(s)
Comments: 2
Kudos: 89





	1. Chapter 1

Sitting on the bed in her own motel room, Katie was reading up on the current case displayed on her laptop when her cellphone vibrated underneath her thigh, digging out and looking down to see her boyfriend calling. She couldn't tell him what she actually did for a living because she doesn't want him to think she's absolutely bonkers, so the first thing that came out of her mouth when he asked was family business. She told him that she and her older brothers went around the country to help people. It was a form of the truth, but she changed the subject before he could ask any more questions she didn't want to answer. 

"Hey, babe," Katie said, setting aside the laptop, a wide smile on her face. "How's it going back in Kansas?"

"Boring without you," he replied, she could wear the grin in his voice. "Are you almost done in Texas? I could really use your... touch."

Katie laughed as she moved down on the bed, resting her head on the pillow so she was staring up at the ceiling. "How about my voice?" she offered, clearly piquing his interest.

"Are you suggesting what I think you're suggesting, Ms. Winchester?" He tsked, causing her to roll her eyes.

"Do you want it or not?" she questioned.

Silence was on the other side until she heard him breathe. "It's not as good as the real thing, but it'll work." He cleared his throat. "Where do we start?"

"Well, obviously we both have to get naked," she stated, grinning widely. "Taking my clothes off now." Holding the phone in between her cheek and shoulder, she took her free hands down to her jeans and unbuttoned them, sliding them off. She could hear the rustling on the line, a little relief to hear that he was doing it, too. Soon, she was completely naked on her bed.

"I'm already hard," he said, sighing. "Damn, Katie, you're good."

"Make yourself harder, sir," she told him, placing her index and middle finger onto her clit. "I'm just imagining you here with me, that it's your fingers and not my own."

He moaned as she shook, rubbing her fingers harder. "Keep talking, Katie," he begged. "I love your voice."

"I can't wait to get home to you," she continued. "I'll put my mouth on your dick and give you the best damn blowjob you've ever received." She moaned into her phone as he did the same, the sound coming from both of you didn't let her hear the motel door slowly being pushed open, closing gently with a click. "Fuck, babe. Harder." She moved her two fingers and penetrated herself, pulling them in and out as best she can at the awkward angle. It wasn't nearly as satisfying as the real thing, she knew he was right about that. Her eyes fluttered close as she fingered herself harder with her boyfriend's moans in her ear.

She was completely oblivious to her older brother, Dean, standing near the door. He palmed the bulge in his jeans and furrowed his eyebrows as he watched his little sister fuck herself. Was he getting hard? Yes, he was.

He unbuttoned his pants and pulled his dick out, giving it a stroke as her moans reached his ears. She said her boyfriend's name as she was preparing herself to orgasm, but all Dean could picture her saying was his name and he wanted to hear it for himself. 

Dean slowly stalked over to her bed, reaching over and pulling out her hand. She released a gasp as Dean put his own fingers into her, pistoning in and out of her at a speed she never thought a human could perform, a moan escaping the back of her throat as Dean smirked at her, running his thumb along her clit as he fucked her.

"Oh, fuck," Katie moaned, shaking as Dean licked his lips. "Shit, babe. That feels so good."

Her boyfriend groaned next to her ear, "Cum for me, babe."

With Dean's rough fingers pounding away inside of her, she had no problem doing just that. Katie released a scream as her juices flowed out and onto her brother's hand, Dean slowing down as he prepared to pull out. The phone fell onto the bed as Katie panted. She could slightly hear her boyfriend's grunts as he came as well, laughing as he called out to her.

"I'm here, babe," Katie breathed as she moved her head closer to the phone, her eyes not seeming to leave Dean's cock as he moved to rub it. "What's next?"

"I'm ready for round two," he said to her, laughing a bit more. "I already started."

Katie squeezed her eyes shut. She had wished he was done, but she knew better. He was always ready for round two, and so was she. "Okay," Katie said, watching Dean position himself by her pussy. "Let me get some assistance."

"Ooh, you're going to use a toy?" He seemed giddy of the idea. "I hope it's a good one."

"It looks like it," Katie assured, opening her legs wider as Dean rubbed the tip of his cock against her clit, moving his dick in circles. She moaned loudly. "I'm rubbing the cock on my clit. It feels so fucking good."

Her boyfriend grunted at the same time as Dean released a soft moan, a wide smile on his face as he pushed the head of his cock into her, Katie groaning at the feeling. "What are you doing now, babe?" her boyfriend asked.

"I pushed it into me," she said, her hands gripping the bed sheets tightly. "Now I'm going all the way..." She trailed off as Dean followed her words, bottoming out inside of her, but the wicked smile on his face told Katie that he wasn't just going to stop there. He pulled out suddenly, then rammed back in. "Oh, shit!" she shouted, grunting as Dean pulled the same move multiple times.

"Yes," her boyfriend said in her ear. "Let it fuck you, Katie, just like it was me. Say my name, baby. Say my-"

"Oh, fuck, Dean!" she shouted, eyes widening as she realized what she said.

"What? Dean?" But Dean didn't falter, a wide smile on his face as he continued to ram into his little sister's vagina. "As in your brother Dean?"

Katie couldn't think of anything to say to defend herself, too busy moaning at Dean's dick inside of her. Dean moved his hand over and hung the phone up, saying her name just before he did with a shit-eating grin on his face. "Dean, fuck," Katie breathed, her body moving along with Dean's thrusts. "Why? You're my brother! Why are you- Shit, it feels so good!"

"I walked in on you fingering yourself," Dean panted, "and figured you needed a hand." He grunted as he took both her breasts into his hands, playing with them and making her nipples hard as he continued to ram into her. "You feel better than I thought you would."

"Don't think this is going to be a normal thing," she told him, groaning as he hit her sweet spot. "Right there, Dean, fuck. Oh, my God. I love you."

Dean laughed at her words, going inside her harder. "I think this is going to be a normal thing, sweetheart." He grunted as he moved his hands down to her clit, running his index finger over it. "Come on, Katie, moan for your big brother." She moaned for him, her body compulsing with ecstasy as she came once more. Dean pulled out and rubbed his cock, finishing himself off and watching his cum squirt all over his sister's belly. He slowed his tugging until it came to a stop, smiling at his sister. "I'm sure you're going to want to do this again," he said, winking at her as he pulled his clothes back on and left, going back to his and Sam's room.

She stared at the ceiling, panting. She didn't want to lie, that was the best dick she's ever had.


	2. Chapter 2

Sam watched as Dean pulled away in the Impala after dropping him off at the motel, shaking his head with a sigh as he turned towards the door. He cursed under his breath as he pushed the door open, hoping Dean actually listened to what he wanted from the fast-food restaurant instead of just assuming like he normally does. Sam stopped pushing the door open when he heard his sister, Kiara, on the phone. Why was she in his and Dean's room instead of her own?

Despite himself, he listened to her end of the conversation.

"No, babe, why would I sleep with Dean? He's my brother!" She groaned in annoyance. "No, he just walked in on me- You're not making any sense."

Sam pulled away from the door with furrowed eyebrows. Dean had left sometime in the night and he hadn't come back. Sam just assumed he went out to get something to snack on and snuck back in after Sam dozed off. But that wouldn't explain why he woke up to Dean sneaking back into the room at six in the morning.

He could feel a tightening in his chest as he realized that it was a possibility that what Kiara's telling her boyfriend is a lie. But what is this that he's feeling? Jealousy? No, she's his sister. Why would he be jealous that Dean fucked her? He should be sick to his stomach. And, if he was going to be honest, he is sick. He's sick that Dean fucked Kiara before he did. He just feels as if he needs to prove that he's better than Dean.

Before he could properly process a plan, he closed the door loudly behind him. Kiara jumped at the noise and quickly told her boyfriend she had to go, hanging up on him as she turned to look at Sam. She asked him what was wrong with him, but he just couldn't stop staring at her. He never thought of Kiara like this until now.

"Sammy?" She said his name and the first thing he could think of was wishing that she was saying her name with pleasure instead of confusion.

He crossed the room and brought her lips to his with his hands, her phone falling to the floor. "I want you, Kiara," Sam said into her mouth, his eyes opening to look into hers as he pulled away slowly.

"What the fuck is happening?" she whispered, but she didn't get an answer before Sam picked her up, Kiara instinctively wrapping her legs around his waist.

Sam connected his lips to hers once more as he made it to his bed, dropping her on there and taking his shirt off as soon as possible. She moved quickly, too, stripping her clothes at the same pace as Sam did. Soon, they were both naked with Sam climbing on top of her. Kiara moaned as he trailed kisses down her stomach until he reached her vagina, his tongue flicking across her clit with no hesitation. She ran her fingers through his hair, gripping it tightly as her body welcomed Sam.

He enjoyed the taste of her, licking her as fast as he could so she could cum on his face, but he didn't feel as if he was doing enough. He shoved an index finger into her, smiling as she groaned. She mentally confessed that his fingers were thicker than Dean's, but the thought immediately left her mind as he added a second finger.

"Fuck," she breathed, pulling Sam's hair. "More."

Sam added the last two fingers at her word, pulling them in and out as he continued to lick her. Her body shook under him and she finally groaned as she sprayed her juices on him, Sam pulling up after she finished to look at her. He moved onto his knees, letting his hard dick flop around. Kiara took the length into her hand and licked the tip of it, looking up at Sam as she took the head into her mouth. Sam's eyes instantly closed at the feeling of warmth, a moan escaping the back of his throat as he placed his hands on the back of her head. He moved his hips, letting his whole cock sit in the back of her throat for a moment before pulling out, giving her a chance to catch her breath. When she took his dick back into her mouth, he moved back and forth faster, fucking her mouth with his dick. He didn't really give her time to breathe as he closed in on an orgasm, her name coming off his tongue in a small whisper. She wasn't even sure she heard it as he pulled her head towards him, bottoming out as he released his cum into her. He made her swallow every last drop before he pulled out.

She gasped to catch her breath as she fell backward, a wide smile on her face as Sam jerked off his cock a few times before positioning himself in front of her pussy. He didn't give her any time to prepare, driving his dick into her with no warning.

"Oh, shit!" she shouted, moaning after. "A little warning would've been nice, Sammy."

He only replied with a grunt as he started moving his hips again, leaning forward so their faces were inches apart. "You're so fucking tight," Sam stated, grinning. "F-Fuck, Kiara, you feel so goddamn good!"

"You're so big, Sam," she said, Sam smiling wider. "Fuck me, Sammy, just fucking fuck me!"

Sam planted a sloppy kiss on her lips before pulling away, using the headboard as support, giving him the ability to move his hips faster. "I want you, Kiara," Sam stated. "Kiara, I just need you." He groaned when her walls squeezed against his dick and she screamed when his dick hit her sweet spot.

"Right there, yeah," she stated breathlessly, laughing. "Oh, fuck. You always dreamed of fucking your sister, Sammy? Naughty."

"I just don't want this to end," Sam stated, laying down on top of her. Her hands went around his back, her nails digging into his skin as he continued to hit her sweet spot. "You're just so perfect."

"Huh, Sam, fuck." She moaned in his ear, giving him a surge of energy as he fucked her faster than he thought he could. "Oh, yes. Sammy, just fuck me like you've never fucked before."

He didn't have time to pull out, emptying his load inside of her. Her eyes widened at the feeling of his cum coursing through her, slapping his shoulder as he pulled up.

"Sam!"

"I'm sorry, Kiara," he panted, smiling a little bit. "You just felt so good, I didn't realize it was going to-"

"Fuck, Sam," she moaned, rolling her eyes.

"I mean, I could do it again."

She looked at him with clear annoyance in her eyes and as if on cue, the motel door opened and closed.

"Alright, Sam, I think I got the actual thing you wanted. And Kiara's stupid chicken-" Dean's voice caught in his throat when he looked up, eyebrows furrowed. Both Sam and Kiara gave him a cheeky, innocent grin as they sat there, as naked as the day there were born. Dean dropped the bags onto the table and placed his hands on his hips. "You two didn't."


	3. Chapter 3

"Don't be mad," Kiara declared, sighing. "It's not like I'm not going to give you another chance, Dean."

Dean shook his head, hands on his hips as he refused to look at Kiara next to Sam, both naked and both not moving to get dressed. "I thought you were trying to get back together with what's-his-face?"

"Yeah, well..." Kiara trailed off into another sigh, furrowing her eyebrows when Sam placed a hand on her thigh. "Now I got two boys who're willing to do me just as much as he was. And, I mean, I'm not going to complain about it. Especially since the two boys are attractive as all hell." She looked at Sam as he slowly moved his hand up her thigh, towards her still-wet pussy. She bit her tongue when his fingers connected with it, her eyes widening as she took a quick look over towards Dean, who was still refusing to look at them.

"I just thought you were mine," Dean stated.

"I can be both of yours." She told Sam to stop under her breath, but he only grinned wickedly as he pushed a finger into her hole. She bit back her gasp and choked a groan as he didn't hesitate to add a second finger so quickly. "You two can take turns." She tried her best not to let the euphoria get the best of her when she was speaking. Dean seems hurt that she fucked Sam, she didn't want to add to the pain. And she wanted Sam to stop.

She grabbed his wrist and tried to yank him out of her, but he fought her hard, which made his fingers go in further and harder. She moaned against her lips as he added a third finger.

"I don't want to share you, Kiara," Dean said, shaking his head. He could see them in the reflection of the window, how his brother's fingers were going in and out of his sister, how she was enjoying it and how she didn't want to make a sound. "I just want you to be mine." He casually palmed the bulge growing in his jeans, squeezing his eyes shut. "This family is fucked up as it is." He looked back up in time to catch the two of them swapping spit, eyebrows furrowed as he quickly turned around. "Really?" he demanded, the two of them immediately pulling apart, but Sam's fingers stayed inside Kiara. "Fuck it." He took his shirt off quickly, beginning to unbuckle his pants as he kicked his boots off.

Kiara squealed as the naked Dean quickly joined the two of them, Sam immediately pulling his fingers out of Kiara and getting into the middle of the bed as he started working his cock. Dean was already hard, replacing Sam's fingers and shoving all four of them into Kiara. She groaned in unison with Dean as she took his length into her hand.

"I can't believe this is going to happen," she breathed, a wide smile on her face. "I always dreamed of a threesome, just never with my own brothers."

"You're so fucking wet," Dean whispered, licking his lips.

"We used you, Kiara," Sam said, jerking his cock as he watched his brother finger her. "It's your turn to use us. Whatever it is you want, we'll do it."

Kiara's eyes widened as she watched Dean nod his head in agreement to Sam's words, but furrowed his eyebrows in confusion she took her hand away from his cock. "Alright, then, boys," she stated, grinning. "I want the two of you two give each other a blow job."

Dean slowly took his fingers out of her and looked over at Sam, sharing a look. "What? That's not what we-"

"Ah, Dean," she interrupted, pointing her finger towards her vagina. "No more of this until you do as I say."

The men groaned heavily as they got into position, Kiara watching with close eyes as she shoved her own finger into her pussy. 

Sam wrapped his mouth against Dean's head, hesitantly at first, but he soon got over the taste and eventually bottomed out, Dean's dick hitting the back of his throat and nobody ever expected Sam Winchester to have such a damn good gag reflex. Dean was more skeptical than Sam, but he seemed to be enjoying the blow job a lot. Kiara's moan caused Dean to look over at her, watching her finger herself and knowing that that could be him soon, so he shook his head and got over whatever was holding him back. He licked Sam's tip, the moan coming from Sam caused vibrations on his dick that made Dean moan in return.

Dean took Sam's cock into his mouth and started bobbing his head, moaning along with his brother as Kiara's groans reached their ears.

Sam used his hand as extra rubbage, making Dean moan and groan louder. "Fuck, Sammy, who knew you were so good at this," Dean stated after popping his brother's dick out of his mouth. "Oh, shit. I'm so close."

"Stop," Kiara demanded, Sam removing himself from Dean. She looked at Sam, but spoke to Dean as she said, "I want you to finish in me."

"But you'll get-"

"Just do it." She removed her hand from herself as Dean scrambled to get to her.

She motioned for Dean to lay down as she rubbed Sam's cock while she waited for Dean to get comfortable. Dean's dick stood up front and center and she released Sam so she could climb on top of Dean. She made eye contact with Sam as she positioned herself over Dean, grabbing the older Winchester's dick to guide it into her pussy. She moaned as she bottoms out, her eyes never leaving Sam as he pathetically rubbed his own cock.

"Oh, Dean," Kiara moaned as Dean held onto her hips, grunting. She started bouncing up and down, Sam watching her breasts fly. "Ugh, fuck me. Fuck me, Dean, good and hard." Dean started moving his hips against Kiara's rhythm, meeting her with a hard thrust when she came back down. "Oooh, Sammy, you getting jealous over there?"

As Kiara and Dean moaned in sync, Sam couldn't help but confess to himself that he was actually getting jealous. Watching Dean fuck her when he should, it was something he couldn't stand, but he did. He rubbed his cock at barely half the pace Dean's fucking her. Her moans reached his ears as she said Dean's name when she should be saying his. And when Dean finished in her like she wanted (which was just revenge for Sam finishing in her when she didn't want it), he felt even madder.

Sam climbed over to them and positioned his cock at her entrance.

"What're you doing?" she asked, trying to get off of Dean's dick, but Sam kept her there by keeping a hard grip on her shoulder. "Sam!" She gasped when he easily shoved his hard cock inside of her, rubbing against Dean's and everybody moaned.

"Holy fuck," Dean breathed, laughing a little bit. Sam made Kiara lay back on Dean so she was facing the ceiling, keeping both of their dicks in there all the while. "Shit."

Sam started moving his hips, pulling back and slamming in. Kiara didn't break eye contact with Sam as he fucked her with Dean's cock still in there, Dean moaning in her ear as she shook with euphoria. Sam grunted as he started picking up the pace, watching as Dean's hands went to her breasts and started rubbing the nipple. Sam picked up one of her legs and let it rest on his shoulder while he took his free hand and started rubbing her clit as fast as his arm would let him.

"Holy shit!" she screamed, clearly not caring about the neighbors. She moaned louder than the brothers have ever heard her, a smile on both of their faces as Sam continued penetrating her, his dick hitting her sweet spot as it rubbed against Dean. "Oh, yes. Fuck, Sam. Oh, you guys feel so fucking good right now."

"I'm going to cum again, Sammy, let me out," Dean begged, but Sam just kept hammering away. "Sammy." He moaned Sam's name, a sound Sam thought he wouldn't enjoy but he did. Dean moaning Sam's name only made him go faster, trying to make Dean finish inside her once again. "Sammy, please. Fuck." Kiara came all over their dicks first, which was unexpected because Sam thought Dean was going to lose.

Dean came the second Kiara was done, his hips shaking as he released more of his seed inside of her, the movement causing his dick to move for the first time since Sam forced his up there. Sam groaned as the newer feeling, looking over at Dean to see his eyes closed and his face in total euphoria. Sam finished last, bottoming out as much as he can as he emptied out inside of her. He laid over her as he orgasmed, Kiara speechless at the feeling now.

A few moments passed and they were all still tangled together, Sam is the first one to pull his dick out. He looked down at Dean's dick still inside his sister, smiled, then climbed off the bed.

"Let's do it again sometime," Kiara said as she lazily rolled off of Dean, his dick popping out of her. "That was fun."


End file.
